1-Methylpiperazine → 5-Fluoro-6-(4-methylpiperazinyl)isatin

HRID 1756558Notes

Reaction equation

HRID 1756558 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1F)[NH:7][C:6](=[O:12])[C:5]2=[O:13].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[NH:7][C:6](=[O:12])[C:5]2=[O:13]

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 19263085,6-difluoro-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 193907095-Fluoro-6-(4-methylpiperazinyl)isatinYield 72%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5,6-difluoroisatin (1.0 g, 5 mmol) in 50 mL of dimethyl sulfoxide was added N-methylpiperazine (5.47 g, 50 mmol). The mixture was stirred for 4 h at room temperature and the crude reaction mixture was diluted with ethyl acetate. The organic solution was washed with saturated sodium bicarbonate. The organic layers were separated and concentrated to give the title compound in 72% yield: mp 150° C. (dec); 1H NMR (300 MHz, DMSO-d6)δ 10.8 (br s, 1H), 7.3 (d, 1H), 6.4 (d, 1H), 2.25 (s, 3H), 2.2 (m, 4H), 2.1 (m, 4H).

Workup

  1. customthe crude reaction mixture
  2. washThe organic solution was washed with saturated sodium bicarbonate
  3. customThe organic layers were separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe055647377f40788f46b7a0bc724a93
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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